Profile

Derek Horton

Professor Emeritus
Department of Chemistry

  • Additional Positions at AU

    Isbell Professor of Chemistry
  • Derek Horton received his degrees from the University of Birmingham in England, was on the Chemistry faculty at Ohio State University until 1992, and held visiting professorships in France and Germany. He held the Isbell Chair of Carbohydrate and Natural Product Chemistry at American University between 1993 and 2009, where he taught courses on carbohydrate and natural product chemistry. His research is on the organic, biochemical, and technological aspects of carbohydrates. He was a founder of the international journal Carbohydrate Research and is editor of the annual book series Advances in Carbohydrate Chemistry and Biochemistry. He serves on the International Commission for Biochemical Nomenclature and several committees of the American Chemical Society, and has published about 500 articles, books, and patents in the carbohydrate field.
  • Degrees

    PhD, DSc, Birminghan (UK)
    FRIC, Royal Institute of Chemistry, London
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Scholarly, Creative & Professional Activities

Research Interests

Research of the Horton group is primarily concerned with the organic and biological chemistry of carbohydrates, both simple sugars and glycoconjugates, from the standpoints of structure, synthesis, and reactivity.

Synthetic Interests

Development of reactions of high specificity for use in polyfunctional biological molecules: Specific deoxygenation reactions. Amination at predetermined positions. Specific oxidation; enols in stereochemically controlled synthesis. Use of acetylenes in synthesis. Preparative photochemical reactions. Specifically labelled sugars as biochemical probes. Reactions of dithioacetals.

Structural modification of antibiotics: Application of reactions for pinpointing structural alteration of carbohydrate antibiotics (especially aminocyclitols) to modify biological activity. Also, modifications of nucleoside structure.

Antitumor compounds: Synthesis of compounds showing in vivo antitumor activity, especially anthracycline antibiotics. Synthesis of daunosamine analogs, glycosidic coupling to natural and synthetic anthracyclinones, evaluation in tumor screens, cardiotoxity determination, design of pro-drugs. Coupling of nucleic acid bases and analogues to sugars of modified functionality (aminated, acyclic-chain, deoxy, aminoacylated) and stereochemistry. Structural characterization of products and biological evaluation against tumor lines and viruses.

Polysaccharides of biological importance: Specific structural modification of natural polysaccharides to provide synthetic anticoagulants, antilipemic agents, and polymers of interest in technology, and modified substrates for studies on mode of enzyme action. Application of synthetic transformations to such molecules as amylose, cellulose, chitin, and cycloamyloses, to introduce specific repeating functionality such as amino groups, oxidized or reduced groups, deoxy functions, or stereochemical variants.   

Structural Work

Conformational analysis of polysubstituted tetrahydropyran and tetrahydrofuran rings - The effect of multiple substitution (OH and OR, systematically as a function of configuration) on the static and dynamic conformational properties of the molecule in solution. Influence of cations and anions; relation to enzyme-catalyzed reactions of sugars. Techniques: 1H NMR and 13C NMR spectroscopy; correlation with X-ray crystallography. The role of acyclic sugars in chemical and biochemical reactions. Development of quantitative treatments of steric and electronic interactions in multi-substituted systems. Correlations with optical rotatory behavior.

Lipopolysaccharide antigens of gram-negative bacteria: Structural characterization of antigenic lipopolysaccharides. Determination of structural units and linkage-sequence in polysaccharide moiety, to establish nature of antigenic site at the molecular level. Chemical synthesis of the antigenic-determinant groups and their conjugation to carrier proteins (for synthesis of artificial antigens) and to solid-support media to furnish affinity adsorbents used in isolating and studying homologous antibodies. Development of monoclonal antibody-based therapeutic vaccines. Major tools: GLC-mass spectrometry, high-field NMR.

Heparin, the natural blood anticoagulant: Details of the fine structure of this complex sulfated glycosaminoglycan: its component units, position of sulfation, structure of the heparin-protein linkage in the biological source. Nature of the thrombin- and antithrombin-binding sites. Chemical synthesis of orally active agents of high antithrombotic and low hemorrhagic activity. Techniques of macromolecular chemistry and biochemistry; chromatography.  Physical methodology for structural analysis of complex carbohydrates - Structures of oligosaccharides (including antibiotics), extension to polysaccharides, by 1H NMR and 13C NMR and mass spectrometry.   

Reactivity Studies

Ring-closure reactions of carbohydrates under kinetic and thermodynamic conditions: Competition between hydroxl groups in ring closure of sugars; influence of stereochemical and conformational factors. Rationale for design of synthesis. Understanding of steric control in biological reactions of carbohydrates.

Enzymology of modified polysaccharides: Evaluation of the action of hydrolase enzymes (amylases, cellulases) and transglycosylases on synthetic products to provide: (a) information on the specificity and mode of action of the enzymes, (b) fragment molecules useful in synthesis, structural work, and biochemistry, and (c) technological leads such as protection of wood from rotting, promotion of biodegradability.

Relative reactivity of hydroxyl groups in sugars and polysaccharides: Determination of the site and extent of competitive substitution reactions, such as acylation and alkylation, in simple sugar derivatives and in polysaccharides. Implications in synthesis, in technology (textiles, foods), and in biochemistry.

Honors, Awards, and Fellowships

Claude S. Hudson Award in Carbohydrate Chemistry, ACS, 1972

Alumni Distinguished Teaching Award, Ohio State University, 1980

Wolfrom Award, ACS Carbohydrate Division, 1988

Alexander von Humboldt Senior Scientist Award, German Federal Republic, 1989

Haworth Medal, Royal Society of Chemistry, 1990

Morley Medal, ACS Cleveland Section, 1991

Patterson-Crane Award, ACS Dayton and Columbus Sections, 1997

Hillebrand Prize, Chemical Society of Washington, 1997

Elected Fellow of the American Chemical Society, 2010

Elected Fellow of the Royal Society of Chemistry, 2011

 

Recent Publications

Foreword to: Click Chemistry in Glycoscience: New Developments and Strategies, Zbigniew J. Witczak and Roman Bielski (Editors), Wiley, in press (April 2013).

Carbohydrate Nomenclature, Derek Horton, in G. C. K. Roberts (Ed), Encyclopedia of Biophysics, Springer Berlin Heidelberg, 2013, pp 232--236.

Carbohydrate Antibiotics, Derek Horton, in G. C. K. Roberts (Ed), Encyclopedia of Biophysics, Springer Berlin Heidelberg, 2013, pp. 213--214.

Anomeric Effect,  Derek Horton, in G. C. K. Roberts (Ed), Encyclopedia of Biophysics, Springer Berlin Heidelberg, 2013, pp. 93--94.

Advances in Carbohydrate Chemistry and Biochemistry.  D. Horton, Editor, Elsevier Academic Press, Amsterdam and San Diego, Vol. 68, 2012, xii + 535 pp.

Enzymatic Conversions of Starch, P.. Tomasik and D. Horton, Adv. Carbohydr. Chem. Biochem., 68 (2012) 59—436.

Advances in Carbohydrate Chemistry and Biochemistry.  D. Horton, Editor, Elsevier Academic Press, Amsterdam and San Diego, Vol. 67, 2012, xii + 277 pp. 

Advances in Carbohydrate Chemistry and Biochemistry.  D. Horton, Editor, Elsevier Academic Press, Amsterdam and San Diego, Vol. 66, 2011, x + 328 pp.

Advances in Carbohydrate Chemistry and Biochemistry.  D. Horton, Editor, Elsevier Academic Press, Amsterdam and San Diego, Vol. 65, 2011, x + 303 pp..

Foreword, in Carbohydrate Chemistry:  Proven Synthetic Methods, Pavol Ková?, Editor, Taylor and Francis, Boca Raton, FL, Volume 1, 2011, xii—xiv.

Advances in Carbohydrate Chemistry and Biochemistry.  D. Horton, Editor, Elsevier Academic Press, Amsterdam and San Diego, Vol. 64, 2010, xiii + 547 pp.

Inhibitory activity of four demethoxy fluorinated anthracycline analogs against five human-tumor cell lines.  Derek Horton and Anakshi Khare, Bioorg. Med. Chem. Lett., 20 (2010) 6179—6181.

Advances in Carbohydrate Chemistry and Biochemistry.  D. Horton, Editor, Elsevier Academic Press, Amsterdam and San Diego, Vol. 63, 2010, xii + 435 pp. 

Advances in Carbohydrate Chemistry and Biochemistry.  D. Horton, Editor, Elsevier Academic Press, Amsterdam and San Diego, Vol. 63, 2010, xii + 435 pp.

Advances in Carbohydrate Chemistry and Biochemistry.  D. Horton, Editor, Elsevier Academic Press, Amsterdam and San Diego, Vol. 62, 2009, xiii + 407 pp.

The Development of Carbohydrate Chemistry and Biology.  Derek Horton.  In H. G. Garg, M. K. Cowman, and C. A. Hales (Eds.),  “Carbohydrate Chemistry, Biology and Medical Applications,” Elsevier, 2008, pp 1—28.

Advances in Carbohydrate Chemistry and Biochemistry.  D. Horton, Editor, Elsevier Academic Press, Amsterdam and San Diego, Vol. 61, 2007, xii+ 436 pp.

Synthesis of the four 1-(1-deoxy-D-pentitol-1-yl)thymines and conformational properties of the acyclic sugar chain.  Scott M. Vejcik and Derek Horton,Carbohydr. Res., 342, 806--818 (2007).

Synthesis of 3'-C-substituted thymidine derivatives by free-radical techniques:  scope and limitations. Derek Horton, Kuangmin Chen,  Zaesung No, and Howard C. Lee. Carbohydr. Res., 342, 259—267 (2007).

Synthesis and reactivity of nonstabilized diazo sugars.  Michael S. Alexander and Derek Horton, Carbohydr. Res., 342, 31—43 (2007).

Please see also Derek Horton Publications (PDF), complete list.